Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 38, 2024 - Issue 11
99
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Study on the metabolism of natural sesquiterpene lactones in human liver microsomes using LC-Q-TOF-MS/MS

, , &
Pages 1855-1863 | Received 22 Feb 2023, Accepted 13 Jun 2023, Published online: 24 Jun 2023

References

  • Barda C, Ciric A, Soković M, Tsoukalas M, Skaltsa H. 2018. Phytochemical investigation of Crepis incana Sm. (Asteraceae) endemic to southern Greece. Biochem Syst Ecol. 80:59–62. doi: 10.1016/j.bse.2018.06.009.
  • Barda C, Grafakou M-E, Tomou E-M, Skaltsa H. 2021. Phytochemistry and evidence-based traditional uses of the genus Achillea L.: an update (2011–2021). Sci Pharm. 89(4):50. doi: 10.3390/scipharm89040050.
  • Bohlmann F, Zdero C. 1982. Sesquiterpene lactones and other constituents from Tanacetum parthenium. Phytochemistry. 21(10):2543–2549. doi: 10.1016/0031-9422(82)85253-9.
  • Cai W, Zhang JY, Dong LY, Yin PH, Wang CG, Lu JQ, Zhang HG. 2015. Identification of the metabolites of Ixerin Z from Ixeris sonchifolia Hance in rats by HPLC–LTQ-Orbitrap Mass Spectrometry. J Pharm Biomed Anal. 107:290–297. doi: 10.1016/j.jpba.2015.01.004.
  • Darbahani M, Rahaie M, Ebrahimi A, Khosrowshahli M. 2022. The effects of several abiotic elicitors on the expression of genes of key enzymes involved in the parthenolide biosynthetic pathway and its content in feverfew plant (Tanacetum parthenium L.). Nat Prod Res. 36(23):6132–6136. doi: 10.1080/14786419.2022.2055555.
  • Douglas JA, Smallfield BM, Burgess EJ, Perry NB, Anderson RE, Douglas MH, Glennie VL. 2004. Sesquiterpene lactones in Arnica montana: a rapid analytical method and the effects of flower maturity and simulated mechanical harvesting on quality and yield. Planta Med. 70(2):166–170.
  • Freund RRA, Gobrecht P, Fischer D, Arndt HD. 2020. Advances in chemistry and bioactivity of parthenolide. Nat Prod Rep. 37(4):541–565. doi: 10.1039/c9np00049f.
  • Ghantous A, Gali-Muhtasib H, Vuorela H, Saliba NA, Darwiche N. 2010. What made sesquiterpene lactones reach cancer clinical trials? Drug Discov Today. 15(15–16):668–678. doi: 10.1016/j.drudis.2010.06.002.
  • Gillette JR. 1971. Factors affecting drug metabolism. Ann N Y Acad Sci. 179:43–66. doi: 10.1111/j.1749-6632.1971.tb46890.x.
  • Grafakou ME, Barda C, Heilmann J, Skaltsa H. 2022. In vitro cytotoxic and anti-inflammatory activities of sesquiterpene lactones from Centaurea papposa (Coss.) Greuter. Nat Prod Res. 36(12):3211–3215. doi: 10.1080/14786419.2021.1955882.
  • Grafakou ME, Barda C, Karikas GA, Heilmann J, Skaltsa H. 2021. Cajamolides A-N: cytotoxic and anti-inflammatory sesquiterpene lactones from the leaves of the Panamanian rain forest Calea jamaicensis (L.) L. Bioorg Chem. 116:105351. doi: 10.1016/j.bioorg.2021.105351.
  • Grafakou ME, Djeddi S, Tarek H, Skaltsa H. 2018. Secondary metabolites from the aerial parts of Centaurea papposa (Coss.) Greuter. Biochem Syst Ecol. 76:15–22. doi: 10.1016/j.bse.2017.11.005.
  • Jiang Z, Peng C, Huang W, Wu B, Zhang D, Ouyang H, Feng Y, Yang S. 2019. A high throughput three-step ultra-performance liquid chromatography tandem mass spectrometry method to study metabolites of atractylenolide-III. J Chromatogr Sci. 57(2):163–176. doi: 10.1093/chromsci/bmy098.
  • Jürgens FM, Behrens M, Humpf H-U, Robledo SM, Schmidt TJ. 2022. In vitro metabolism of helenalin acetate and 11α,13-dihydrohelenalin acetate: natural sesquiterpene lactones from Arnica. Metabolites. 12(1):88. doi: 10.3390/metabo12010088.
  • Kasenova S, Atazhanova GA, Sagintaeva Z, Kasenov BK, Kishkentaeva AS, Adekenov SM. 2016. Thermodynamic properties of sesquiterpene lactone grossheimin. Russ J Phys Chem. 90(8):1521–1524. doi: 10.1134/S0036024416080112.
  • Koukoulitsa E, Skaltsa H, Karioti A, Demetzos C, Dimas K. 2002. Bioactive sesquiterpene lactones from Centaurea species and their cytotoxic/cytostatic activity against human cell lines in vitro. Planta Med. 68(7):649–652. doi: 10.1055/s-2002-32893.
  • Kreuzer A, Kerres S, Ertl T, Rücker H, Amslinger S, Reiser O. 2013. Asymmetric synthesis of both enantiomers of arteludovicinolide A. Org Lett. 15(13):3420–3423. doi: 10.1021/ol401473v.
  • Liscombe DK, Louie GV, Noel JP. 2012. Architectures, mechanisms and molecular evolution of natural product methyltransferases. Nat Prod Rep. 29(10):1238–1250. doi: 10.1039/c2np20029e.
  • Majdi M, Liu Q, Karimzadeh G, Malboobi MA, Beekwilder J, Cankar K, Vos R, Todorović S, Simonović A, Bouwmeester H. 2011. Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum parthenium L. Schulz Bip.). Phytochemistry. 72(14–15):1739–1750. doi: 10.1016/j.phytochem.2011.04.021.
  • Maria-Eleni Grafakou: Agatonovic-Kustrin S, Morton DW. 2018. The current and potential therapeutic uses of Parthenolide. In Studies in natural products chemistry. Elsevier, Netherlands, 58:61–91. doi: 10.1016/B978-0-444-64056-7.00003-9.
  • Merfort I. 2011. Perspectives on sesquiterpene lactones in inflammation and cancer. Curr Drug Targets. 12(11):1560–1573. doi: 10.2174/138945011798109437.
  • Moujir L, Callies O, Sousa PMC, Sharopov F, Seca AML. 2020. Applications of sesquiterpene lactones: a review of some potential success cases. Appl Sci. 10(9):3001. doi: 10.3390/app10093001.
  • Papakosta K, Grafakou ME, Barda C, Kostopoulos IV, Tsitsilonis O, Skaltsa H. 2020. Cytotoxicity and anti-cancer activity of the genus Achillea L. Curr Med Chem. 27(41):6910–6925. doi: 10.2174/0929867327666200505092514.
  • Saosathan S, Khounvong J, Rungrojsakul M, Katekunlaphan T, Tima S, Chiampanichayakul S, Berkland C, Anuchapreeda S. 2021. Costunolide and parthenolide from Champi Sirindhorn (Magnolia sirindhorniae) inhibit leukemic cell proliferation in K562 and molt-4 cell lines. Nat Prod Res. 35(6):988–992. doi: 10.1080/14786419.2019.1610752.
  • Schepetkin IA, Kirpotina LN, Mitchell PT, Kishkentaeva АS, Shaimerdenova ZR, Atazhanova GA, Adekenov SM, Quinn MT. 2018. The natural sesquiterpene lactones arglabin, grosheimin, agracin, parthenolide, and estafiatin inhibit T Cell Receptor (TCR) activation. Phytochemistry. 146:36–46. doi: 10.1016/j.phytochem.2017.11.010.
  • Schmidt TJ. 2018. Structure-activity and activity-activity relationships of sesquiterpene lactones. In: Sülsen V, Martino V, editors. Sesquiterpene lactones: advances in their chemistry and biological aspects. Springer International Publishing AG, Switzerland. p. 349–371.
  • Sokovic M, Ciric A, Glamoclija J, Skaltsa H. 2017. Biological activities of sesquiterpene lactones isolated from the genus Centaurea L. (Asteraceae). Curr Pharm Des. 23(19):2767–2786. doi: 10.2174/1381612823666170215113927.
  • Sowjanya G, Ganapaty S, Sharma R. 2019. In vitro test methods for metabolite identification: A review. Asian J Pharm Pharmacol. 5(3):441–450. doi: 10.31024/ajpp.2019.5.3.2.
  • Yu Z, Chen Z, Li Q, Yang K, Huang Z, Wang W, Zhao S, Hu H. 2021. What dominates the changeable pharmacokinetics of natural sesquiterpene lactones and diterpene lactones: a review focusing on absorption and metabolism. Drug Metab Rev. 53(1):122–140. doi: 10.1080/03602532.2020.1853151.
  • Zaiter L, Bouheroum M, Benayache S, Benayache F, León F, Brouard I, Quintana J, Estevez F, Bermejo J. 2007. Sesquiterpene lactones and other constituents from Matricaria chamomilla L. Biochem. Syst. Ecol. 35(8):533–538. doi: 10.1016/j.bse.2007.03.008.
  • Zenger K, Agnolet S, Schneider B, Kraus B. 2015. Biotransformation of flavokawains A, B, and C, chalcones from Kava (Piper methysticum), by human liver microsomes. J Agric Food Chem. 63(28):6376–6385. doi: 10.1021/acs.jafc.5b01858.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.